Triacetoxyperiodinane → HCID 9979610, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-hydroxy-cyclopentyl)-N-pyrazin-2-yl-propionamide (prepared as in Example 38, 60 mg, 0.142 mmol) in methylene chloride (10 mL) was treated with Dess-Martin periodinane (132.5 mg, 0.312 mmol). The reaction mixture was stirred at 25° C. for 2 h. The reaction mixture was then diluted with methylene chloride (10 mL) and washed with a 1M aqueous citric acid solution (10 mL). The pH of the aqueous layer was adjusted to 5. The aqueous layer was then extracted with methylene chloride (20 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50–100% ethyl acetate/hexanes) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-N-pyrazin-2-yl-propionamide (45 mg, 75%) as an off-white solid.

Provenance & Evidence